UA79003C2 - Indolin phenylsulfonamide derivatives - Google Patents

Indolin phenylsulfonamide derivatives Download PDF

Info

Publication number: UA79003C2
Authority: UA; Ukraine
Prior art keywords: methyl; hydrogen; alkyl; means hydrogen; mmol
Prior art date: 2002-07-03

Application number

UAA200500952A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Bayer Healthcare Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-07-03

Filing date

2003-06-30

Publication date

2007-05-10

2003-06-30 Application filed by Bayer Healthcare Ag filed Critical Bayer Healthcare Ag

2007-05-10 Publication of UA79003C2 publication Critical patent/UA79003C2/uk

Links

ZFJPEIIOZIZJAB-UHFFFAOYSA-N benzenesulfonamide;2,3-dihydro-1h-indole Chemical class C1=CC=C2NCCC2=C1.NS(=O)(=O)C1=CC=CC=C1 ZFJPEIIOZIZJAB-UHFFFAOYSA-N 0.000 title 1
-1 phenoxy, benzyloxy Chemical group 0.000 claims description 60
229910052739 hydrogen Inorganic materials 0.000 claims description 57
239000001257 hydrogen Substances 0.000 claims description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
239000012453 solvate Chemical class 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000003003 spiro group Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 102
238000000034 method Methods 0.000 abstract description 86
238000011282 treatment Methods 0.000 abstract description 15
208000029078 coronary artery disease Diseases 0.000 abstract description 5
208000032928 Dyslipidaemia Diseases 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
208000024172 Cardiovascular disease Diseases 0.000 abstract description 2
102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 abstract description 2
230000003213 activating effect Effects 0.000 abstract description 2
108091008765 peroxisome proliferator-activated receptors β/δ Proteins 0.000 abstract description 2
230000003389 potentiating effect Effects 0.000 abstract 1
238000011321 prophylaxis Methods 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
239000002904 solvent Substances 0.000 description 62
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
239000000243 solution Substances 0.000 description 49
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 47
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 46
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
239000000203 mixture Substances 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
239000003480 eluent Substances 0.000 description 28
239000003112 inhibitor Substances 0.000 description 28
230000015572 biosynthetic process Effects 0.000 description 25
238000003786 synthesis reaction Methods 0.000 description 25
239000000047 product Substances 0.000 description 24
239000000126 substance Substances 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
238000003756 stirring Methods 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 21
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000002994 raw material Substances 0.000 description 18
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 18
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
229960000583 acetic acid Drugs 0.000 description 17
238000005481 NMR spectroscopy Methods 0.000 description 16
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
239000002253 acid Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000005160 1H NMR spectroscopy Methods 0.000 description 14
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 14
239000013543 active substance Substances 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 12
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
230000003993 interaction Effects 0.000 description 12
239000003208 petroleum Substances 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
210000004369 blood Anatomy 0.000 description 11
239000008280 blood Substances 0.000 description 11
102000005962 receptors Human genes 0.000 description 11
108020003175 receptors Proteins 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
239000005557 antagonist Substances 0.000 description 10
239000002585 base Substances 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 9
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
239000000556 agonist Substances 0.000 description 9
235000019253 formic acid Nutrition 0.000 description 9
239000008103 glucose Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000011592 zinc chloride Substances 0.000 description 9
235000005074 zinc chloride Nutrition 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
229910052784 alkaline earth metal Inorganic materials 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
239000012300 argon atmosphere Substances 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
102000004877 Insulin Human genes 0.000 description 6
108090001061 Insulin Proteins 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
238000001816 cooling Methods 0.000 description 6
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229940125753 fibrate Drugs 0.000 description 6
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229940125396 insulin Drugs 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
239000000523 sample Substances 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
239000008096 xylene Substances 0.000 description 6
HTFXWAOSQODIBI-UHFFFAOYSA-N 2-benzyl-1,3-dihydropyrrolo[3,4-c]pyridine Chemical compound C1C2=CC=NC=C2CN1CC1=CC=CC=C1 HTFXWAOSQODIBI-UHFFFAOYSA-N 0.000 description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
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229910052783 alkali metal Inorganic materials 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
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239000011734 sodium Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
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QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 4
SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
108090000854 Oxidoreductases Proteins 0.000 description 4
102000004316 Oxidoreductases Human genes 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
239000003513 alkali Substances 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
239000003146 anticoagulant agent Substances 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
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230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
229940044601 receptor agonist Drugs 0.000 description 4
239000000018 receptor agonist Substances 0.000 description 4
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229960001522 ximelagatran Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

UAA200500952A 2002-07-03 2003-06-30 Indolin phenylsulfonamide derivatives UA79003C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10229777A DE10229777A1 (de)	2002-07-03	2002-07-03	Indolin-Phenylsulfonamid-Derivate
PCT/EP2003/006896 WO2004005253A1 (de)	2002-07-03	2003-06-30	Indolin-phenylsulfonamid-derivate

Publications (1)

Publication Number	Publication Date
UA79003C2 true UA79003C2 (en)	2007-05-10

Family

ID=29796112

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200500952A UA79003C2 (en)	2002-07-03	2003-06-30	Indolin phenylsulfonamide derivatives

Country Status (26)

Country	Link
US (1)	US20060100230A1 (pt)
EP (1)	EP1519919A1 (pt)
JP (1)	JP2005535649A (pt)
CN (1)	CN1678581A (pt)
AR (1)	AR040352A1 (pt)
AU (1)	AU2003246638A1 (pt)
BR (1)	BR0312549A (pt)
CA (1)	CA2491477A1 (pt)
DE (1)	DE10229777A1 (pt)
EC (1)	ECSP055524A (pt)
GT (1)	GT200300135A (pt)
HN (1)	HN2003000196A (pt)
HR (1)	HRP20050108A2 (pt)
IL (1)	IL165924A0 (pt)
MA (1)	MA27316A1 (pt)
MX (1)	MXPA05000133A (pt)
MY (1)	MY134641A (pt)
NO (1)	NO20050579L (pt)
NZ (1)	NZ537486A (pt)
PE (1)	PE20040645A1 (pt)
RU (1)	RU2328485C2 (pt)
TW (1)	TW200418794A (pt)
UA (1)	UA79003C2 (pt)
UY (1)	UY27878A1 (pt)
WO (1)	WO2004005253A1 (pt)
ZA (1)	ZA200500013B (pt)

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2002
- 2002-07-03 DE DE10229777A patent/DE10229777A1/de not_active Withdrawn
2003
- 2003-06-30 RU RU2005102592/04A patent/RU2328485C2/ru not_active IP Right Cessation
- 2003-06-30 EP EP03762547A patent/EP1519919A1/de not_active Withdrawn
- 2003-06-30 BR BR0312549-1A patent/BR0312549A/pt not_active IP Right Cessation
- 2003-06-30 CA CA002491477A patent/CA2491477A1/en not_active Abandoned
- 2003-06-30 MX MXPA05000133A patent/MXPA05000133A/es unknown
- 2003-06-30 US US10/519,125 patent/US20060100230A1/en not_active Abandoned
- 2003-06-30 CN CNA038209446A patent/CN1678581A/zh active Pending
- 2003-06-30 UA UAA200500952A patent/UA79003C2/uk unknown
- 2003-06-30 WO PCT/EP2003/006896 patent/WO2004005253A1/de not_active Application Discontinuation
- 2003-06-30 JP JP2004518622A patent/JP2005535649A/ja not_active Withdrawn
- 2003-06-30 NZ NZ537486A patent/NZ537486A/en unknown
- 2003-06-30 AR ARP030102373A patent/AR040352A1/es not_active Application Discontinuation
- 2003-06-30 AU AU2003246638A patent/AU2003246638A1/en not_active Abandoned
- 2003-07-01 MY MYPI20032474A patent/MY134641A/en unknown
- 2003-07-02 GT GT200300135A patent/GT200300135A/es unknown
- 2003-07-02 UY UY27878A patent/UY27878A1/es not_active Application Discontinuation
- 2003-07-02 TW TW092118027A patent/TW200418794A/zh unknown
- 2003-07-02 PE PE2003000668A patent/PE20040645A1/es not_active Application Discontinuation
- 2003-07-02 HN HN2003000196A patent/HN2003000196A/es unknown
2004
- 2004-12-22 IL IL16592404A patent/IL165924A0/xx unknown
2005
- 2005-01-03 EC EC2005005524A patent/ECSP055524A/es unknown
- 2005-01-03 ZA ZA200500013A patent/ZA200500013B/en unknown
- 2005-01-03 MA MA28032A patent/MA27316A1/fr unknown
- 2005-02-02 NO NO20050579A patent/NO20050579L/no not_active Application Discontinuation
- 2005-02-02 HR HR20050108A patent/HRP20050108A2/hr not_active Application Discontinuation

Also Published As

Publication number	Publication date
RU2328485C2 (ru)	2008-07-10
TW200418794A (en)	2004-10-01
US20060100230A1 (en)	2006-05-11
CA2491477A1 (en)	2004-01-15
MXPA05000133A (es)	2005-04-11
WO2004005253A1 (de)	2004-01-15
MA27316A1 (fr)	2005-05-02
AU2003246638A1 (en)	2004-01-23
AR040352A1 (es)	2005-03-30
PE20040645A1 (es)	2004-10-29
ECSP055524A (es)	2005-03-10
UY27878A1 (es)	2004-02-27
CN1678581A (zh)	2005-10-05
ZA200500013B (en)	2006-03-29
DE10229777A1 (de)	2004-01-29
HRP20050108A2 (hr)	2006-04-30
JP2005535649A (ja)	2005-11-24
MY134641A (en)	2007-12-31
NO20050579L (no)	2005-02-02
BR0312549A (pt)	2005-04-26
EP1519919A1 (de)	2005-04-06
NZ537486A (en)	2006-07-28
RU2005102592A (ru)	2005-07-10
HN2003000196A (es)	2004-11-22
IL165924A0 (en)	2006-01-15
GT200300135A (es)	2004-03-17

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